Private only

Vermont Bike Tour

Quintessential New England at Leaf-Peeping Peak

4 days / 3 nights Level: 3Price From: $3,895Collection: Classic

Tour Highlights

  • Cycle beside the Ottauquechee River and past historic Taftsville Covered Bridge to a cheese tasting at Thistle Hill Farm
  • Visit Vermont’s most well-known microbrewery, Long Trail, for a tour and tasting
  • Go leaf-peeping from the seat of a bicycle, feeling the warmth of the fall sun
  • Watch a glassblowing demonstration and dine at the riverfront flagship location of glassmaker Simon Pearce


Local sharp cheddar, the finest grades of maple syrup, hand-churned ice cream, and seasonal farm-fresh produce


Apple cider and craft beer

As featured in:
Print Itinerary
  • Day 1

    Ottauquechee River Loop

    Your guides will greet you upon arrival in Woodstock and begin with a bike fitting and safety talk. Our first spin in the Green Mountain State takes us on wooded roads dappled with sunlight streaming through colorful canopies of leaves. Midway through our ride, we’ll pedal up to Thistle Hill Farm for a tasting of its famed Tarentaise cheese, inspired by cheesemaking traditions in the Savoie department of the French Alps. After sampling to our heart’s content, we continue cycling astride the Ottauquechee River, passing the historic Taftsville Covered Bridge before making our way back into Woodstock. A satisfying lunch at a quaint local café is followed by an afternoon of free time. This evening, toast to the days ahead over locally sourced dishes at the Inn’s celebrated Red Rooster restaurant.

    Meals: Lunch / Dinner
    Destinations: Pomfret, Woodstock
    Accomplished: 26 miles / 42 km, elevation gain: 564 meters
    Accommodations: Woodstock Inn

  • Day 2

    Long Trail Loop

    After an energizing breakfast, pedal south towards Plymouth on a route lined with rolling hills, sleepy farms, and babbling brooks. This quintessential Vermont village provides us with a glimpse of gentler times a hundred years ago, and we’ll sample delicious cheeses from the Plymouth Cheese Factory, one of the oldest in the country. After our tour and tasting, hop back on the and start the scenic ride towards Bridgewater. As we slowly descend toward the Queechee River, the views seem to get better and better. To cap off a delicious day, we’ll raise our pint glasses at Long Trail Brewery.

    Meals: Breakfast / Lunch / Dinner
    Destinations: South Woodstock, Felchville, Plymouth
    Accomplished: 45 miles / 72 km, elevation gain: 916 meters
    Accommodations: Woodstock Inn

  • Day 3

    Hidden Farm to Mount Ascutney

    Today we set off along the banks of the Ottauquechee River until we meet Skunk Hollow Road. Flanked by the towering Green Mountains, we’ll pedal south on scenic roads that stream through sleepy Vermont towns to the base of Ascutney Mountain. From here, head back to Woodstock with a stop at the South Woodstock Country Store for a mouth-watering lunch prepared by fellow cycling enthusiasts. Tonight, we revisit Quechee for an evening at Simon Pearce Glassworks. Shop for stemware, pottery, pitchers, and bowls, or simply watch the glassblowers at work. Our dinner here beside the river is as artful as the hand-blown glass shimmering all around us.

    Meals: Breakfast / Lunch / Dinner
    Destinations: South Woodstock, Windsor, Brownsville, Hartland, Quechee
    Accomplished: 35 miles / 56 km, elevation gain: 685 meters
    Accommodations: Woodstock Inn

  • Day 4

    South Woodstock Farm Ride

    After your final breakfast in the region, join your guides for a short, scenic loop ride to cement your memories with a little leaf peeping! The morning light is our favorite for fall photos, so be sure to snap a few before spinning back to the hotel and bidding farewell to this beautiful corner of the world.

    Meals: Breakfast
    Destinations: South Woodstock
    Accomplished: 10 miles / 16 km, elevation gain: 287 meters

DuVine itineraries may be subject to slight route changes, hotel substitutions, and other modifications.

Arrival Details

Airport City: Boston, Massachusetts Pick-Up Location: Lobby of the Woodstock Inn Pick-Up Time: 9:00 am
Departure Details

Airport City: Boston, Massachusetts Drop-Off Location: Woodstock Inn Drop-Off Time: 1:00 pm


  • Thoughtfully selected accommodations that reveal the true character of the region
  • Luggage transfers


  • Daily breakfasts, all lunches, nutritious snacks, and après velo cocktails
  • 3 gourmet dinners at our favorite local restaurants and renowned culinary establishments
  • Carefully selected local wine, beer, or spirits with every meal


  • Wine tastings and activities as outlined in the tour itinerary
  • Entrance fees to historic sites, museums, parks, and all other exclusive events
  • Gratuities for baggage, porters, and hotel service


  • Top-of-the-line bicycle selection
  • Bike helmet
  • Complimentary DuVine gear, including a custom cycling jersey, DuVine t-shirt, water bottle, and drawstring bag
  • GPS in most destinations


  • Expert bilingual guides with extensive local knowledge
  • Support vehicle that follows the day’s route, distributes refreshments, and offers lifts
  • Pick-up and drop-off before and after your tour from predetermined meeting points
  • Daily bike maintenance to ensure optimal performance

See our FAQs page for answers to common questions.

See FAQs